Steven Woods

A broker who gives the house cut back

Most people in finance spend a career learning where the money hides. Steven Woods spent his learning who it hides from. Today he runs Stirlingshire Investments out of an office on West 38th Street in Manhattan, a FINRA-member, SEC-registered broker-dealer he built around a heresy: that an advisor should keep 100% of the asset management fees and commissions they generate, with zero expenses skimmed on the way out.

That is not a marketing line. It is the entire architecture. Stirlingshire calls itself a Hybrid Broker-Dealer, a splice of the full-service model the wirehouses run - Morgan Stanley, Merrill Lynch, JP Morgan - and the discount model that came after. Woods kept the parts that serve people and cut the parts that serve the firm. The firm passed FINRA and SEC review and began its beta in 2022. The clearing partner, APEX, looked at the model and negotiated a warrant to buy 3% of the company in lieu of charging clearing fees. When your vendor would rather own a slice than bill you, you have built something unusual.

The question that runs everything

Woods keeps returning to four words: "How do we make this better?" He says it about advisor pay, about client choice, about the quiet habits the industry would rather not discuss. He has a name for the worst of them - closet indexing, where a manager hugs the benchmark and counts not-losing-money as a job well done. He is not interested in not-losing. He is interested in the structure underneath, the one that decides who pays whom and for what.

His client model is the cleanest expression of it. He calls it advice on demand, and it offers three doors. Behind the first: self-directed trading at zero commission, for the people who want to drive. Behind the second: professional recommendations you only pay for when they actually make you money. Behind the third: full management, for the people who want to hand over the wheel entirely. The point is that you stop having to choose between expensive guidance and no guidance at all. You pick the relationship you want and pay for exactly that.

Where the conviction came from

The conviction is earned, not theoretical. Woods started in finance at 26 with a GED, an intern at a boutique firm cold-calling for about $500 a day. That is where he says he met "the nefarious side of the industry" up close, before he had any power to change it. He was good at the work - good enough to become an advisor producing millions a year in annual revenue. And good enough to do the arithmetic that most top producers never say out loud: that he was, in effect, "paying half a million dollars to go to work," handing a fortune to a firm for the privilege of generating it. The absurdity of that line item is the seed of Stirlingshire. He left a lucrative seat to build the firm he wished had existed when he was dialing.

He has since stacked executive programs onto the GED - the General Management Program at Harvard Business School, the Advanced Management and Leadership Programme at Oxford. The credentials are real, but they are not the story. The story is a man who carries both the cold-call and the classroom, and trusts the cold-call more.

Borrowing Robinhood's playbook, not its product

Ask Woods what he is modeling and he will tell you plainly: Robinhood. Not the app, the move. Robinhood did not invent a better commission - it took the commission to zero and forced an entire industry to follow. Woods wants to do that to advisor compensation. His five-year target is to hire 5,000 advisors and, by sheer gravity, pressure the independent firms into offering a genuine 100% payout instead of the asterisked versions they advertise now. He believes the better advisors spot phoniness instantly, that you keep talent with superior products and pay rather than golden handcuffs, and that broker protocol flexibility is a feature, not a threat. If your people can leave easily and stay anyway, you have built the right thing.

On technology, he is deliberately unromantic. AI at Stirlingshire reads a portfolio in seconds and hands the analysis to a human, who still makes the call. The machine is an efficiency multiplier, not a fiduciary, and Woods is content to keep it there until the regulators say otherwise. It is a telling restraint from a man whose whole pitch is disruption: he will break the pay model overnight and let the robots wait their turn.

And then there is the line that tells you what kind of founder he is. Asked about the prize, Woods said improving "the world in the financial services world" matters more to him than making his "next billion dollars." Founders say things like that all the time. Fewer of them have already walked away from a half-million-dollar cover charge to prove it.